


Oh dear me!

by Anonymous



Category: Supernatural
Genre: Dildos, First Time, Markers, Masturbation, Object Insertion, Object Penetration, Sexual Experimentation, Vegetables, What is this shit???, idk anymore
Language: English
Status: Completed
Published: 2019-10-28
Updated: 2019-10-28
Packaged: 2021-01-05 20:47:50
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,735
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21214838
Author URL: https://archiveofourown.org/
Summary: Sam gets curious with his ass





	Oh dear me!

**Chapter 1**

-15- 

It starts off really innocent. Sam’s only fifteen years old when he gets this bright idea of sticking something up his ass. It starts off with his markers. The bright neon coloured markers. He’s in the middle of his biology assignment about the human body and he’s struck with this idea. 

He’s not quite why he suddenly gets this bright idea from. It’s probably from the fact that his brother and dad were out doing some hunting stuff. 

He ruffled out of his shorts, grabbed oil from the kitchen and leaned down on the floor of the cheap kitchen motel. He spread his legs, and soaked the neon markers generously in oil and began to rub the markers on his ass crack. 

Sam shivered as he felt the marker get caught by the entrance skin of his asshole. Then he placed a little more pressure and then a little harder and harder until he felt his muscles gave way. 

He squeezes his ass muscles and removes his hand away from the marker. His ass feels a little heavy and he can feel the marker hanging. 

He gives an experimental squeeze. Sam’s eyebrows furrowing. It doesn’t hurt. But it’s an uncomfortable feeling in his ass. He pushes the marker all the way in until he hits the end cap of the marker then he pulls it back out and in. 

Until he grows bored of it. There’s no stimulation. 

He eventually gets bored of it and decides to switch method by jerking off in the bathroom and washing himself. Ready for dinner. 

He feigns innocence when Dean shoots him a suspicious look and stared at the greasy floor. It’s not like they’re planning to stay long anyways. The hotel cleaning services could easily clean the grease off the floor. 

-16- 

Sam doesn’t stop playing the game of shoving things up his ass. He’s not sure why he even continued to shove things inside his ass when he felt no sexual excitement to it. It was boring and dry and just not exciting at all. But to his amazement, his biggest record was two neon markers. He had also tried with other objects. 

He tried with a pencil, pen and even a ruler, which he obviously didn’t go far with. For safety reasons. 

He doesn’t want to risk losing a marker inside his ass so he moves on to something else. He gets the bright idea of using vegetables for his sexual curiosity. 

To be far, it was all Dean’s fault. He had shoved the whole grocery shopping chore on him and now he just brought those long english cucumbers. 

Of course, he had to hide it as soon as he got home. His family didn’t eat greens at all and if they found out he had brought cucumbers, he was sure they were going to interrogate him. 

It’s only after Dean and Dad had retired to bed and Sam counting their snores that he finally got the courage to get off of the bed. 

He tiptoed into the kitchen, taking out the cucumber from the freezer. He gasped. It was cold to touch. He froze, listening intently to the snoring in the bedroom. 

No movement. 

He released a breath of relief. He pulled out the cooking oil, coating the cucumber in oil. He slipped off of his shorts, and bent down on all fours, positioning the head of cucumber at his hole. 

He placed a little bit of pressure. His one long year of playing with his ass was showing results. The head of the cucumber easily slipped past his entrance muscles. 

He continued to push through. It was only until he hit something that caused him to spasm that he stopped pushing. His eyes rolled back, mouth gaping open. 

What was that?

He bit his lips, tugging on the cucumber stuck in his ass. He pulled it back out and pushed it back in and there it was. Sam could taste blood in his mouth. 

His toes curling. He could feel drool escaping his mouth. Fuck. That felt so good. He squeezed his eyes shut, resuming the same motion. He glanced down at his cock, it was erect and proudly red. 

He hissed, feeling himself getting closer and closer to release. He barely held back a shout, his cock spurting white semen all over the kitchen tiles. His mind reeled back to the noise in the bedroom. 

“Sam, you alright?” Dean groggily asked. 

“Yeah,” Sam gritted his teeth, roughly pulling out the cucumber from his ass. He grabbed the kitchen towel to wipe his semen off of the floor. “Just using the bathroom.”

Sam was thankful Dean didn’t get up. 

-17-

Sam doesn’t indulge himself in those sexual acts as much. He’s still pretty much straight. He likes girls. He likes how they smell, and how they look. Personally, if he was feeling adventurous, he was willing to use something up his ass. But the last incident had been during Christmas. 

But instead of cucumber, he had used a carrot. It was a little unsatisfactory but he still did get off on it. 

This year, he’s on the baseball team as the manager. He didn’t really want to do the whole running around sweating. He was more for throwing out orders and plus, he got all the ladies sticking to him like glue. 

It was a win-win solution. 

Plus a third win. 

Sam had been assigned to do a count all the items in the gym while the team was playing with the opposition team. Sam was alright with it. 

He needed a little breather. 

Of course, that’s also when he gets this amazing idea of trying to get the baseball bat up his ass. 

He was never one to back down from a challenge. He does it. It’s a little harder than he had ever experienced because he had no lubrication to cover the baseball bat in. Instead, he gives the bat the best blowjob the bat will ever experience. 

He wraps his mouth on the wooden handle, gagging a little at the salty taste. He pushes as far as he could, which isn’t far, before he feels the temptation of trying to throw up. 

He resorts to licking the sides down. Sam’s a little embarrassed to say but he’s pretty much a professional at going on all fours. 

He discards his shorts, and spreads his legs. If anyone saw him, they would see how obscene he looked. Thankfully, no one was around. 

He pressed the base of bat on his hole, it easily slipped inside, and he continues to push through until he hits halfway on the bat. 

His inside clenches around the bat painfully but Sam can’t help satisfy moan from escaping his lips. 

He plays with his ass like this for a while until he decides to use the head of the bat, the largest part, to enter him first. 

His ass is very resistant to giving entrance but a little more forceful push and it just breaks his hole and pushes in. 

Sam’s a little worried that his ass has split open but the painful pleasure he feels brims his head with ecstasy. He continues to pump the bat in and out, almost like it’s ramming at him with the intention of leaving his ass gaping open. 

That shoves Sam over and he spills white semen all over the gym equipment. 

He’d have to leave the windows open overnight. 

-18-

It’s when Sam is legally eighteen that he enters a well known sex shop. He’s not at all embarrassed like most shoppers. He’s been studying this for a couple of years now. 

A pretty lady with black lipsticks and a stud earring comes over to help him. She doesn’t question him when he asks her for the biggest and widest dildo they got. 

Sam goes home with a 12 inch and 8.5 wide dildo in a black plastic bag. The cashier gave him a knowing smile and Sam tucks the plastic under his arms for safety measures. 

The dildo was pretty expensive but it was for a reason. It could be used to remain in one place. 

Sam left it on the dining chair, it was an obscene sight. The dildo was at least like Sam’s forearm. Sam, by no means, isn’t a small man. 

He swallows slowly, getting down all the way to his shorts. He lubed the dildo up and pushed his loose boxers aside and he began to lower himself on the thick long dildo. 

He bit his lips, and continued to thrust himself down until he was fully sheathed the dildo inside his ass. He could barely composed himself when the door slammed open. 

His mouth gaping when he tried to pull up from the dildo. He squeezed his eyes, and pushed himself down and tried to compose himself. He used the table cloth to cover the fact that he wasn’t wearing anything but a boxer. 

“Hey Sammy,” Dean walked in with a bag of diner food. “I got us dinner.”

Sam gave him a weak smile. His insides clenching down on the dildo in nervousness at being found out by his big brother. He pretended to spread the food around, hissing internally when the dildo pinned his prostate down. _Fuck._

His vision blurred, and he readjusted himself. He grabbed his own food and nibbled slowly, hoping Dean would finish and leave him alone in the kitchen. 

“What’s wrong with you?” Dean asked, finishing his second bowl of food. He stood up, walking around and patted Sam on the shoulder. 

Sam jolted, and choked on a cry. His cock spurting in his boxer. _Fuck_. He could feel the wetness growing in his boxer. He just came from being patted by his brother. 

But to be frank, his brother had a strong grip and it only pushed him down further on the dildo which rammed into his prostate. 

“Sam?”

“Nothing. Just feeling a little stressed over school,” Sam managed to respond. 

Dean quirked his eyebrows. Nose wrinkling but nodded his head. He leaned down to ruffled Sam’s hair, “Don’t stress out too much or you’ll end up bald before me.”

Sam bit his lips. If only Dean knew. His little brother was riding on the largest and widest dildo known to men and his ass was probably going to be gaping for days. 

**Author's Note:**

> I honestly, don't know what this is. I don't even know what to say honestly.   
But here we go, Sam basically experimentally fucking himself with anything and everything.  
This is honestly weird...


End file.
